The 2026 Winter Olympics in Milan has become more than just a showcase of athletic excellence—it’s turned into a battleground over free speech, patriotism, and what it means to represent America on the world stage. At the center of the latest controversy is former NFL quarterback Boomer Esiason, who has ignited a fierce national debate with his blunt message to Team USA athletes: stay quiet and focus on your sport.
During his Tuesday morning show “Boomer and Gio” on WFAN, Esiason didn’t mince words when discussing American Olympians who have expressed reservations about representing the United States amid ongoing political tensions.
“Everybody should just pipe down and do their sport and play for our country and respect the flag and respect everything that’s going on,” Esiason declared, his frustration evident.
The comments came after co-host Gregg Giannotti sarcastically asked whether the newly-crowned gold medal-winning figure skating team was “happy to represent America.” Esiason’s response quickly went viral, drawing both support and fierce criticism across social media platforms.
The Athletes Who Sparked the Conversation
The controversy began at a Friday press conference in Milan, when reporters asked Team USA freestyle skiers about what it means to represent their country during the Trump administration’s heightened immigration enforcement operations, particularly ICE raids happening across America.
Hunter Hess, a first-time Olympian competing in freestyle skiing, gave an answer that would soon put him in the crosshairs of criticism from the President himself.
“It brings up mixed emotions to represent the U.S. right now, I think. It’s a little hard,” Hess admitted. “There’s obviously a lot going on that I’m not the biggest fan of, and I think a lot of people aren’t.”
He continued, “For me, it’s more I’m representing my friends and family back home, the people that represented before me, all the things that I believe are good about the U.S. Just because I’m wearing the flag doesn’t mean I represent everything that’s going on in the U.S.”
Chris Lillis, a two-time Olympian and gold medalist competing in aerials, echoed similar sentiments. “I feel heartbroken about what’s happening in the United States,” Lillis said, referencing ICE operations and protests. “I think that, as a country, we need to focus on respecting everybody’s rights and making sure that we’re treating our citizens as well as anybody, with love and respect.”
Trump Enters the Fray
The athletes’ comments didn’t go unnoticed by President Donald Trump, who took to his Truth Social platform to blast Hess.
“U.S. Olympic Skier, Hunter Hess, a real Loser, says he doesn’t represent his Country in the current Winter Olympics,” Trump wrote. “If that’s the case, he shouldn’t have tried out for the Team, and it’s too bad he’s on it. Very hard to root for someone like this. MAKE AMERICA GREAT AGAIN!”
The presidential rebuke added fuel to an already raging fire, with conservative commentators, former athletes, and social media personalities piling on the criticism.
Esiason Joins the Chorus
Esiason, a former NFL MVP who spent 14 seasons in the league and now works as a radio personality, aligned himself firmly with those demanding athletes keep their political views to themselves.
“Yeah, they seemed to be happy to represent America. Not everybody is,” Esiason observed, referring to the figure skating team’s celebration. “But everybody should just pipe down and just do their sport, and play for our country, and respect the flag, and respect everything that’s going on.”
His comments quickly spread across social media, with thousands weighing in on both sides of the debate.
The Backlash to the Backlash
While some applauded Esiason’s stance, many others pushed back hard against the suggestion that athletes should silence themselves.
“Sorry Boom. Freedom of speech is our most cherished and God given right,” one Twitter user responded.
Another wrote: “Respect everything going on? How about they represent the country by competing and stand up for what they believe in. That’s what true Americans do, they stand up for what they believe in using their freedom of speech.”
Critics pointed out the irony of telling people to respect “everything that’s going on” while simultaneously criticizing those who exercise their First Amendment rights to express concern.
“It’s curious that other athletes need to store their opinion but he can express his own,” one commenter noted on the original Facebook post.
Athletes Respond
Hunter Hess issued a measured response on Instagram Monday, defending his right to speak out while reaffirming his patriotism.
“I love my country,” Hess wrote. “There is so much that is great about America, but there are always things that could be better. One of the many things that makes this country so amazing is that we have the right and the freedom to point that out.”
He continued: “The best part of the Olympics is that it brings people together, and when so many of us are divided we need that more than ever. I cannot wait to represent Team USA next week when I compete. Thanks to everyone for their support.”
Olympic snowboarder and two-time gold medalist Chloe Kim also weighed in at a Monday press conference, saying her parents being immigrants makes the issue hit “pretty close to home.”
“I think in moments like these, it is really important for us to unite and kind of stand up for one another,” Kim said. “I think that I’m really proud to represent the United States. The U.S. has given my family and I so much opportunity. But I also think that we are allowed to voice our opinions on what’s going on.”
A Familiar Tension
The controversy echoes longstanding debates about the role of athletes in political discourse. From Muhammad Ali’s Vietnam War stance to Colin Kaepernick’s kneeling protests, the question of whether sports figures should “shut up and play” versus using their platforms for advocacy has divided Americans for generations.
The International Olympic Committee spokesperson Mark Adams declined to comment on Trump’s remarks, stating he wouldn’t “add to the discourse” about statements from any head of state.
As the Milano Cortina Games continue, the debate shows no signs of cooling down. For every voice demanding athletes stay silent and “respect the flag,” there’s another defending their right to speak their conscience—even while wearing it.
The fundamental question remains unanswered: Does true patriotism mean unwavering support for everything happening in your country, or does it mean caring enough to speak up when you believe things could be better?
For now, that debate is playing out not just on the slopes and ice of Italy, but in living rooms, social media feeds, and sports radio shows across America.